Datsyuk won it 4 times but you don't want it named after an active or just retired guy. Ron Francis won it 3X but he's a current GM. Same for MSL - he's a coach.
Bossy won it 3 times - that would ne nice.
Frank Boucher (who?) won it 7 times. Red Kelly 4X, Bobby Bauer, Delvecchio 3X.
as for the Stanley Cup:
https://www.hockey-reference.com/pla...stanlal01.html